The Socrates Express

2. How to Wonder like Socrates

10:47 a.m. On board train No. 1311, en route from Kiato to Athens.

Train of thought. A throwaway expression, a cliché, but a good one. Each one of our thoughts is connected to the next like boxcars on a freight train. They depend on one another for their forward momentum. Every thought, be it about ice cream sundaes or nuclear fusion, is pushed by the previous thought and pulled by the next.

Feelings travel in trains, too. My periodic bouts of melancholia seem as if they come from nowhere, but when I stop and investigate their origin, I discover a hidden causality. My sadness was triggered by a prior thought or feeling, which was triggered by a prior one, which was triggered by something my mother said in 1982. Feelings, like thoughts, never come out of the blue. There’s always a locomotive pulling them along.

I order a pastry and coffee, and my train of thought slows. I think and feel nothing. I am not numb, not exactly. I experience neither happiness nor sadness nor the vast spectrum in between. I am vacant, in a good way. Lulled by the gentle sway of the train, so unlike rough-and-tumble Amtrak, savoring my coffee, not only the taste but the way the mug, warm and with a satisfying heft, nestles in my hand, my anxieties take a holiday. I watch the red roofs and blue Ionian sea glide by as if they, not I, were moving. I gaze out the window at nothing in particular, and I wonder.

I wonder. Two simple words, yet they contain the seeds of all philosophy, and more. All great discoveries and personal breakthroughs began with those two words: I wonder.

Rarely, once or twice in a lifetime if you’re lucky, you stumble across a sentence so unexpected, so plump with meaning, it stops you cold. I found such a sentence buried inside an odd little book called The Heart of Philosophy, by Jacob Needleman. I say odd because at the time I didn’t know philosophy had a heart. I thought it was all head.

Here is the sentence: “Our culture has generally tended to solve its problems without experiencing its questions.”

I put the book down and turned the words over in my mind. I knew they contained an important truth but I didn’t know what. I was confused. How does one experience questions? And what is wrong with solving problems?

A few weeks later, I found myself sitting across from the man who wrote that profound and perplexing sentence. Jacob Needleman is a professor of philosophy at San Francisco State University. Age has slowed his gait. His voice has grown reedy, his skin thin like crepe paper, but his mind remains nimble. Jacob thinks before speaking and, unlike most professors of philosophy, uses words normal people use. Words like “question” and “experience.” The way he combines them, though, is anything but normal.

As we sit on his deck overlooking the Oakland Hills, sipping Earl Grey tea and water infused with lemon, I ask Needleman, in so many words: Are you nuts? We ask questions. Sometimes we pose questions. We might grapple with questions. We do not experience questions. Not even in California.

Needleman is silent. For a long time. So long that I fear he has dozed off. Finally, he stirs, and speaks in a voice so low I have to inch closer to hear.

“It’s rare but it’s possible. Socrates experienced questions.”

Of course. The inscrutable, inevitable Socrates. Philosophy’s patron saint. The King of the Question. Socrates didn’t invent the question, but he altered the way we ask them and, in turn, the answers they yield. You think and act differently because of Socrates, even if you know nothing about him.

Socrates isn’t an easy man to know. Perched so high on the pedestal we’ve erected for him, he’s barely visible. Just a speck. An idea, and a fuzzy one at that.

This is a shame. Socrates was not a speck. He was not an idea. He was a man. A breathing, walking, defecating, lovemaking, nose-picking, wine-drinking, joke-telling man.

An ugly man, too. The ugliest man in Athens, it was said. His nose was broad and flat, his lips full and fleshy, his belly large. He was bald. He had crablike eyes, widely spaced, that endowed him with great peripheral vision. Socrates may or may not have known more than other Athenians (he insisted he knew nothing), but he definitely saw more.

Socrates ate little, bathed rarely, and always wore the same shabby clothes. He walked barefoot everywhere, even in the dead of winter, and with a strange gait, somewhere between a waddle and a swagger. He could go days without sleep, drink without getting drunk. He heard voices—well, a voice. He called it his daemon. “This began when I was a child,” he explained during his trial on charges of impiety and corrupting the youth of Athens. “It is a voice, and whenever it speaks it turns me away from something I am about to do, but it never encourages me to do anything.”

Taken together, Socrates’s peculiar appearance and idiosyncrasies made him otherworldly. “He seems to have entered mankind’s ‘great conversation’ from outside, as if from another planet,” says the contemporary philosopher Peter Kreeft.

This is true, I think, of all philosophers. They possess an otherness that borders on the alien. Even Marcus, a Roman emperor, felt like a misfit. Diogenes, a founder of Cynicism, was the ultimate oddball philosopher. He lived in a barrel, masturbated in public, and in general traumatized the good people of ancient Athens.

This otherness, if not the public masturbation, makes sense. Philosophy is all about questioning assumptions, rocking the boat. Captains rarely rock their own boats. They have too much at stake. Not philosophers. They’re outliers. Aliens.

Socrates was a practitioner of “Crazy Wisdom.” Found in traditions as disparate as Tibetan Buddhism and Christianity, Crazy Wisdom operates on the premise that the path to wisdom is crooked. We must zig before we can zag.

Crazy Wisdom means casting aside social norms and risking ostracism, or worse, to jolt others into understanding. The original shock therapy. No one likes to be shocked, and we often dismiss practitioners of Crazy Wisdom as more crazy than wise. Here is how Socrates’s student Alcibiades describes him: “He will talk of pack-asses and blacksmiths, cobblers and tanners, and he always seems to be repeating the same things so that someone who wasn’t used to his style and wasn’t very quick on the uptake would naturally take it for the most utter nonsense.” Yet, Alcibiades concludes, spend some time truly listening to Socrates and you realize it’s anything but nonsense. “This talk,” he says, “is almost the talk of a god.”

As he pours another cup of Earl Gray, Jacob Needleman tells me about the first question he experienced. He recalls it clearly. Jacob was eleven years old. He and his friend Elias Barkhordian were sitting on a low stone wall in their Philadelphia neighborhood, just as they did several times a week, even on days when the wall was covered in ice and snow.

A year older than Jacob, Elias was tall for his age, “with a big, round face and brilliant, dark eyes.” The two enjoyed chewing over weighty scientific questions, about everything from the movement of electrons to the nature of dreams. These questions intrigued young Jacob, but on this particular day, Elias asked a question that floored him: “Who created God?”

Jacob recalls staring at Elias’s “great, smooth forehead as though I was trying to look into his brain” and realizing that “when he asked that question he was not merely challenging me, but challenging the whole universe. It sent an extraordinary feeling of freedom through me. And I remember saying to myself the words, This is my best friend.”

Jacob Needleman was smitten with the unexpected joy of asking, and experiencing, big questions.

Socrates’s story parallels Jacob’s. The setting, of course, is different—the mean streets of Athens, not Philadelphia—but the trajectory is similar. There was a pivot to a new and unexpected direction and, again, a friend was responsible, in Socrates’s case a young man named Chaerephon. One day, Chaerephon visited the oracle at Delphi and asked the soothsayer a question: Is there any man in Athens wiser than Socrates?

“No,” came the reply. “There is none.”

When Chaerephon relayed the oracle’s words to Socrates, he was flummoxed. No one wiser than he? How could this be? He was a mere stonecutter’s son who knew nothing. Oracles, though, are never wrong, so Socrates decided to investigate. He buttonholed revered Athenians, everyone from poets to generals. Socrates soon discovered these men were not as wise as they thought they were. The general couldn’t tell him what courage is, the poet couldn’t define poetry. Everywhere he turned he encountered people who “do not know the things that they do not know.”

Perhaps the oracle was right, Socrates concluded. Maybe he did possess a kind of wisdom, the wisdom of knowing what he didn’t know. For Socrates, the worst kind of ignorance was the kind that masquerades as knowledge. Better a wide and honest ignorance than a narrow and suspect knowledge.

It is the introduction of this innocent ignorance, this “marvelous new naiveté,” as the philosopher Karl Jaspers puts it, that is Socrates’s greatest contribution to human inquiry, one that still drives the philosophical impulse today.

Socrates was not the first philosopher. Many came before him: Pythagoras, Parmenides, Democritus, and Thales, to name a few. These men turned their gaze heavenward. They strived to explain the cosmos, to penetrate the mysteries of the natural world. Results were mixed. Thales, brilliant in many ways, was convinced all matter in the universe consisted of water. Like Socrates, these philosophers asked questions, but theirs were mainly “what” and “why” questions. What is everything made of? Why do the stars disappear during the day?

These sort of questions didn’t interest Socrates. They were unanswerable, he thought, and, in the end, unimportant. The universe may be fascinating, but it’s not much of a conversationalist, and conversation was what Socrates craved the most.

“Every question is a cry to understand the world,” said the cosmologist Carl Sagan. Socrates would agree, up to a point. Every question is a cry to understand ourselves. Socrates was interested in “how” questions. How can I lead a happier, more meaningful life? How can I practice justice? How can I know myself?

Socrates couldn’t fathom why his fellow Athenians weren’t more interested in these kinds of questions, given their zest for improvement, be it a better way of making statues or practicing democracy. Athenians, it seemed to Socrates, worked tirelessly to improve everything—except themselves. That needed to change, he thought, and he made it his life’s mission to do so.

This marked a major shift in philosophy. No longer is it fuzzy-headed speculation about the cosmos. It is about life, your life, and how to make the most of it. It is practical. Indispensable. As the Roman politician and philosopher Cicero said, “Socrates was the first to call Philosophy down from the heavens, and establish it in the towns, and introduce her into people’s homes.”

Socrates didn’t behave the way we think philosophers must. He displayed no interest in amassing followers. (When students inquired about other philosophers, Socrates happily directed them.) He bequeathed no body of knowledge, no theories or doctrines. He published no dense tomes. In fact, he never wrote a single word. We know Socrates today thanks to a handful of ancient sources, most notably his student Plato.

There is no such thing as “Socratic thought,” only Socratic thinking. Socrates was all means, no ends. We remember the gadfly of Athens today not for what he knew but how he went about knowing it. He cared more about method than knowledge. Knowledge doesn’t age well. Methods do.

Scholars deploy many fancy terms to describe Socrates’s method: the dialectic, the elenchus, inductive reasoning. I prefer a simpler term: talking. I realize that doesn’t sound sophisticated, and probably won’t snag me the Nobel Prize, but it’s true. Socrates talked to people. “Enlightened kibitzing,” the contemporary philosopher Robert Solomon calls it. I love that. It brings philosophy down to earth and elevates it at the same time.

The examined life demands distance. We must step back from ourselves to see ourselves more clearly. The best way to achieve this perspective is through conversation. For Socrates, philosophy and conversation were virtually synonymous.

Socrates talked to all sorts of people: politicians, generals, craftsmen, as well as women, slaves, and children. He talked about all sorts of subjects, too, but only important ones. Socrates wasn’t much for chitchat. He knew life was short and he wasn’t about to waste one second of his allotted time on trivialities. “We are considering how to live the best possible life,” he said, exasperated, to a sophist named Gorgias. “What question can be more serious than this to a person who has any sense at all?”

As much as he loved conversation, Socrates, I think, saw it as simply another tool in his kit. All this enlightened kibitzing had a goal: to know himself. By talking to others he learned how to converse with himself.

Philosophy may be the art of asking questions, but what is a question? Ah, now there’s a question Socrates would love! Take a word everyone knows, everyone thinks they know, and examine it, probe it, poke it from many angles. Shine a bright and unforgiving light on it.

Some twenty-four centuries have elapsed since the barefoot philosopher of Athens roamed the city’s winding, dirty streets and asked questions. We’ve made much progress since then: indoor plumbing, almond milk, broadband. We’ve had more than two thousand years to hone our definitions. We’re pretty good at it, too, judging by the nearly half a million entries in Webster’s Third New International Dictionary. We needn’t dirty our fingers with pages, print or even digital. We can always turn to our faithful aide-de-camp: Siri.

“Hello, Siri.”

“Hey, Eric.”

“I have a question.”

“Ask and you shall receive.”

“What is a question?”

“Interesting question, Eric.”

Then silence. Nothing. I shake my phone. Still nothing. Siri clearly thinks I’m yanking her algorithm, and she’s having none of it. I try a more literal approach.

“Siri: What is the definition of a question?”

“A sentence worded or expressed to elicit information.”

That is accurate, I suppose, but woefully incomplete. Socrates wouldn’t be satisfied. He was a stickler for definitions. He’d find Siri’s answer at once too broad and too narrow. According to Siri’s definition, both the question Have you seen my keys? and What is the meaning of life? exist on an equal plane. Both aim to elicit information, of a sort—and both are difficult to answer, at least in my house—but the information they seek differs so widely as to be of a different kind. The bigger the question, the less interested we are in a reply that provides merely information. What is love? Why does evil exist? When we ask these questions, it is not information we desire but something larger: meaning.

Questions aren’t one-way; they move in (at least) two directions. They seek meaning, and convey it, too. Asking a friend the right question at the right time is an act of compassion, of love. Too often, though, we deploy questions as weapons, firing them at others—Who do you think you are? and at ourselves, Why can’t I do anything right? We use questions as excuses—What difference will it make? and, later, as justification, What more could I have done? Questions, not the eyes, are the true windows to the soul. As Voltaire said, the best judge of a person is not the answers they give but the questions they ask.

Siri’s response captured none of the magic embedded in every good question, the kind Socrates had in mind when he said, “All philosophy begins with wonder.” Wonder, Socrates thought, isn’t something you’re either born with or not, like blond hair or freckles. Wonder is a skill, one we’re all capable of learning. He was determined to show us how.

“Wonder” is a wonderful word. It’s impossible to say it aloud without smiling. It comes from the Old English wundor, meaning “marvelous thing, miracle, object of astonishment.” On one level, to wonder is to seek information, in Siri fashion. I wonder where I can find some dark chocolate? On another level, to wonder is to suspend inquiry, at least momentarily, and simply behold. I wonder what it is about good Belgian chocolate, spiked with sea salt and almonds, that makes my brain dance and my heart sing?

When we question, we are constrained by the topic at hand. Any queries that extend beyond that topic are deemed superfluous and therefore discouraged. Think of a lawyer chided by the judge for veering into “immaterial” lines of questioning, or a high school student reprimanded by her teacher for straying “off topic.”

Wondering is open-ended, expansive. Wondering is what makes us human. That’s been true ever since the first caveman wondered what would happen if he rubbed two sticks together, or dropped a large rock on his head. You never know until you try and you never try until you wonder.

We often conflate wonder with curiosity. Yes, both provide helpful antidotes to apathy, but in different ways. Wonder is personal in a way curiosity is not. You can be curious dispassionately. You can question dispassionately. You cannot wonder dispassionately. Curiosity is restive, always threatening to chase the next shiny object that pops into view. Not wonder. Wonder lingers. Wonder is curiosity reclined, feet up, drink in hand. Wonder never chased a shiny object. Wonder never killed a cat.

Wonder takes time. Like a good meal or good sex, it can’t be rushed. That’s why Socrates never hurried his conversations. He persevered even when his conversers grew weary and exasperated.

Socrates was the original therapist. He tended to answer a question with another question. Unlike a therapist, Socrates did not bill by the hour (he never charged a single drachma for his sessions) and never uttered the words “I’m afraid that’s all the time we have.” He always had more time.

Even when alone, Socrates liked to linger, a friend reports in the Symposium. “He sometimes stops and stands wherever he happens to be.” Another friend recounts an even more unusual episode that occurred when both men served together during the battle of Potidaea.

One time at dawn he [Socrates] began to think something over and stood in the same spot considering it, and when he found no solution, he didn’t leave but stood there inquiring. It got to be midday, and people became aware of it, wondering at it among themselves, saying Socrates had stood there since dawn thinking about something. Finally some of the Ionians, when evening came, carried their bedding out to sleep in the cool air and to watch to see if he’d also stand there all night. He stood until dawn came and the sun rose; then he offered a prayer to the sun, and left.

Good philosophy is slow philosophy. Ludwig Wittgenstein called his profession the “slow cure” and suggested all philosophers greet one another with “Take your time!” I think that’s a fine idea, not only for philosophers but all of us. Rather than “Have a good day” or similarly empty expressions, let’s greet each other with “Take your time” or “Slow down.” Utter these imperatives often enough, and we might actually decelerate.

On some level, I think, we already recognize the cognitive benefits of slowing down. When something makes us stop and think, we say it “gives us pause.” A pause is not a mistake or a glitch. A pause is not a stutter or an interruption. It is not emptiness but a kind of latent matter. The seed of thought. Every pause is ripe with the possibility of cognition, and of wonder.

We rarely question the obvious. Socrates thought this oversight was a mistake. The more obvious something seems, the more urgent the need to question it.

I take it as a given that I want to be a good father. It is so self-evident it hardly requires stating.

Not so fast, Socrates would say. What do you mean by “father”? Are you speaking in strictly biological terms?

“Well, no. Actually, my daughter is adopted.”

Ah, so a “father” is something more than biological?

“Yes, absolutely.”

What defines a father, then?

“Someone, a male, who cares for a young child.”

So if I take your daughter to, say, Delphi for a few hours am I her father?

“No, of course not, Socrates. Being a father entails a lot more than that.”

What is it then, that separates a male adult who cares for a child from a male adult worthy of the title “father”?

“Love. That is what makes a father a father.”

Very good. I like that answer. Of course, we need to define “love,” but we’ll save that for another time. Now, you say you want to be a “good” father?

“Yes, I do, very much so.”

What do you mean by good?

Here I confess I haven’t a clue. Only the vaguest notions—inchoate, cartoonish images—spring to mind: ice cream sundaes, band recitals, soccer practice, homework coaching, college tours, jokes when she’s feeling down, and even if she’s not, sleepover pickups, yin to my wife’s yang. Good cop, mostly.

These are fine images, Socrates would say, but what do they add up to? You don’t really know what you mean when you say “good father,” do you? And, with a final twist of the philosophical knife, Socrates would suggest that until I knew, really knew, what I mean by “good father,” I couldn’t possibly become one. I was chasing a ghost.

For Socrates, all misdeeds, such as bad parenting, are committed not out of malice but ignorance. If we understood the ramification of our missteps—not only for our children but for ourselves, too—we wouldn’t commit them. A genuine understanding of a particular virtue leads to virtuous behavior. Automatically. To know—truly know—what it means to be a good father is to be one.

It was Take Your Child to Work Day. I always dread this day. Other parents take their children to shiny, serious offices with conference rooms and phone banks and gravitas. My office (one of them anyway) is a local diner called Tastee. The food does not live up to its name, but the booths are large, the waitresses friendly, and the coffee infinite. This year, for the first time, my daughter agreed to tag along.

How to break through to a thirteen-year-old is a mystery the world’s great philosophers have yet to solve. If a tree falls in the woods and her friends don’t share it on Snapchat, it didn’t fall. Sonya showed no interest in my work, in philosophy, in anything, it seems, beyond her teenage world. I suspected the only reason she agreed to go to work with me that morning was so she could skip a day of school.

As we picked at our breakfast—heart-healthy omelet for me, chocolate chip pancakes for her—I stared down the great void that is parenthood. I felt inadequate and, worse, invisible. What would Socrates do?

He would ask questions, of course. I’d been wrestling with one question in particular, a sort of meta question. Is that old saw true—is there really no such thing as a stupid question? I put this question to my daughter, who, with a barely perceptible twitch of her left eyebrow, indicated: I have registered your question, Father, and deemed it unworthy of a response, so I shall now return to my pancakes and Snapchat.

I persisted, like Socrates. “Is there such a thing as a stupid question?” I repeated, louder.

She lifted her head from the screen and thought for a while. At least I surmised she was thinking. Then, to my amazement, she spoke.

“Yes,” she said. “A stupid question is one you already know the answer to.” And with that she returned to her pancakes and her phone and her adolescent pique.

Not for the first, or last, time had she surprised me. She was right. Unless you happen to be a prosecutor, asking a question you already know the answer to is indeed stupid. We do this more often than you might think, and in various ways. We might ask a question to show off our knowledge, or to elicit information that buttresses an unswerving, unexamined conviction we already hold.

For Socrates, none of these qualified as serious questions. A serious question steps into uncharted waters. A serious question carries risk, like striking a match in a dark room. You don’t know what you’ll find when the room illuminates—monsters or miracles—but you strike the match anyway. That’s why serious questions are uttered not confidently but clumsily, hesitantly, with all the gangly awkwardness of a teenager.

For Socrates, nothing was more important, or courageous.

Professor Jacob Needleman pours me another glass of lemon-infused water, his hands slow but steady. The ice cubes clink as they strike the glass. The California light has grown softer, the colors richer, as the sun dips low.

I ask Needleman more about himself. He takes a deep, wheezy breath and transports me back to the 1940s Philadelphia of his youth. Elias and he continued their philosophical gabfests on the stone wall, though with decreasing frequency. One day when Jacob phoned Elias’s home, his mother answered and, in a peculiar voice, said he was resting. Jacob knew something was wrong well before he heard the word “leukemia.”

He recalls one of the last questions he experienced with Elias. “I wonder what happens to a person when we fall asleep,” Jacob asked his friend. “Where does he go?”

For the first time, Elias had no answer. He died shortly before his fourteenth birthday.

Death, especially an unnaturally early one, has a way of focusing the mind. Questions flooded Jacob’s. Why Elias and not him? What should we do with this short time allotted? He received no satisfying answers from his parents or his teachers or his rabbi. So he turned to Socrates and philosophy.

“Why philosophy?” I ask.

“Why do you love something? You feel called. Called to the ultimate questions. Who are we? What are we? Why are we here? Human beings need meaning. So, yes, it was a calling.”

Jacob’s parents weren’t thrilled with his calling. “As the older son, I was obliged by God to become a doctor,” he deadpans. Jacob did become a doctor, only not the medical kind. He earned a PhD in philosophy. He still recalls the first time he was introduced socially as “Dr. Needleman” in his mother’s presence. She interrupted to point out, “He’s not the kind of doctor that does anybody any good, you know.”

Needleman spent the rest of his life proving her wrong. He amassed academic accolades and promotions, always eager to reach a wider audience. He couldn’t fathom why these “ultimate questions” received so little attention. “Our culture has no place where the ultimate questions are honored as questions. Every institution and social form we have is devoted either to solving problems or providing pleasure,” Needleman says.

He pauses, letting his words loiter in the soft California air. He’s right, I realize. Solving a problem before you experience it is like trying to cook a meal before buying groceries. Yet so often we reach for the quickest solution, or the most expedient pleasure. Anything to avoid sitting with our ignorance.

My eyes wander across the Oakland Hills, a dusty brown this time of year. My ears register the pleasant jingle of a nearby wind chime, mingling with a wordless presence that fills the space between me and Jacob Needleman, and connects us.

Socrates was suspicious of the written word. It lies lifeless on the page, and travels in only one direction, from author to reader. You cannot talk to a book, not even a good book.

That’s why I decide not to read Plato’s dialogues but to listen to them. I download the lot. I’m not sure what the ancient Greek word for “megabyte” is, but it’s an awful lot of them.

The dialogues become the soundtrack of my life. I listen as I ride the train and as I drive my daughter to soccer practice. I listen as I pump my legs on the elliptical. I cook to Socrates and I drink to Socrates. I wake to Socrates and I go to sleep to Socrates.

The dialogues feature Socrates and one or more interlocutor wrestling with the meaning of, say, justice or courage or love. These are no dry treatises. They are full-throated conversations, at turns contentious and, to my surprise, funny, too. “A wisdom full of pranks,” as Nietzsche put it.

A conversation with Socrates was often infuriating and disorienting, as one character from the Dialogues, Nicias, attests. “Anyone who is close to Socrates and enters into conversation with him is liable to be drawn into an argument, and whatever subject he may start, he will be continually carried round and round by him, until at last he finds that he has to give an account both of his present and past life, and when he is once entangled Socrates will not let him go until he has completely and thoroughly sifted him.”

Another interlocutor complained that Socrates reduced him to a “mass of helplessness” and compares the philosopher to a “torpedo fish” (also known as an electric ray) that numbs people’s minds.

Conversing with Socrates was frustrating the way conversing with an inquisitive five-year-old is frustrating.

Can we have ice cream for dinner?

No.

Why?

Because ice cream isn’t good for you.

Why?

Because it contains sugar.

Why is sugar bad for you?

Because it is stored in the fat cells of your body.

Why?

Because it just is! Now go to your room.

The child’s questions irk us not because they are silly but because we are incapable of answering them adequately. The child, like Socrates, unmasks our ignorance, and while that may be beneficial in the long run, in the short run it’s annoying. “If you do not annoy anyone, you are not a philosopher,” says Peter Kreeft.

I read that and perk up, hopeful. I have it on good word, and from multiple sources, that I am indeed annoying. World-class. I see other similarities with Socrates. The outlier status. The paunch. The wandering, wondering mind. The love of talk.

Where we part ways, though, is persistence. I tend to walk away from a fight, real or imagined. Not Socrates. He displayed great courage. Fighting in the siege of Potidaea, in 432 BC, he demonstrated remarkable strength and stamina, saving the life of his friend Alcibiades.

In the philosophical arena, too, Socrates was unrelenting. He was an unsparing auditor, demanding people account not only for their beliefs but for their lives. You couldn’t wiggle out of a debate with Socrates. He saw through the smoke screen of obfuscation favored by intellectual posers, then and now. Look at you, a general, who doesn’t know what courage is. A priest who can’t tell me what piety is. A parent who doesn’t know what love is.

The goal was not to humiliate but to illuminate, to facilitate a kind of intellectual photosynthesis. Socrates as gardener. He loved nothing more than “planting a puzzle in a mind and watching it grow.”

This puzzle planting was tricky business. Nobody likes having their ignorance exposed, especially so publicly, and many of the dialogues grew heated. “I don’t understand you, Socrates, so I wish you’d ask someone who did,” said one of his annoyed companions in a dialogue called Gorgias. “You are a tyrant, Socrates. I wish you’d either bring an end to this argument or get someone else to argue with you.” Sometimes more than strong words were exchanged. “Men pummeled [Socrates] with their fists and tore his hair out,” reports the third-century-AD biographer Diogenes Laertius.

Socrates annoyed others for a good cause: better vision. Socrates as optometrist. People walk around with faulty eyeglass prescriptions. Naturally, this lapse affects how they see, and what they see. They have mistaken their distorted view of reality as the only view. Worse, they don’t even know they’re wearing glasses. They stumble through the day, bumping into furniture, tripping over people, all the while blaming the furniture and the people. Socrates thought this was silly, and unnecessary.

The sun has turned a glowing crimson, and a slight chill has crept into the air. Jacob Needleman and I have been talking for hours but neither of us has tired of this enlightened kibitzing. We turn to the subject of false beliefs.

The philosopher, Needleman suggests, is like a burly bouncer at the Nightclub of Ideas.

“A philosopher says to his opinions, ‘You are my opinions. How did you get in here? You didn’t ask me. I didn’t examine you. Yet I believe you. You’re taking over my life.’ ”

I think of my opinions and how they colonize my mind. Like all wily colonizers, they trick me into believing I invited them. Did I? Or did they show up unannounced, these ideas of others, and dress themselves in my clothing?

I circle back to that intriguing, beguiling notion of “experiencing questions.” What does he mean?

Jacob explains that he distinguishes ordinary questioning from “deep questioning.” Ordinary questioning skates along the surface, like Siri. Deep questioning is slow and immersive.

“If I really live a question, let it haunt me, then this state of deep questioning is transformative in itself.”

“Live the question?”

“Yes, live the question. Have it in the back of your mind a lot of the time. Living a question. Not just trying to fix it. Too often we jump to the solution.”

This sounds good, makes me want to spend the rest of my days living questions, but what about answers? Where do they fit in? This is the rap on philosophy: that it’s all talk, endless questions and no answers. The train that is always departing, never arriving.

Not true, says Needleman. Philosophy is definitely interested in the destination, but the journey can’t be rushed. That is the only way to ensure you arrive not merely at clever answers but “answers of the heart.” The other kind, answers of the head, are not only less satisfying but, in the deepest sense, less true.

Arriving at answers of the heart demands not only patience but a willingness to sit with your ignorance. Staying with the doubt, the mystery, rather than rushing to solve the problem, to check off another item on your endless to-do list. This takes time, and courage. Others will mock you. Let them, says Jacob Needleman, and Socrates, too. Ridicule is the price of wisdom.

A while ago, I was speaking with my friend Jennifer. To clarify: I was speaking; she was listening, as I relayed my usual catalog of worries.

I suffer from a distribution problem, I told her. I have enough of any given attribute, but it’s distributed unevenly. Hair, for instance. I’ve got plenty on my chest, and in my nostrils, but not nearly enough on my head.

Success, though, is more problematic. That is not a distribution problem, I explained, but a genuine shortage. “I am not,” I told her, “successful enough.”

Jennifer paused the way people do when they are either about to say something profound or are plotting an escape strategy. Fortunately, Jennifer’s pause was the former.

“What does success look like?” she said.

“What does success look like?” I said.

“Yes, what does success look like?”

Normally, when you parrot a question back to someone they feel obliged to elaborate, to connect the dots for you. Not Jennifer. My question boomeranged and hit me upside the head. What does success look like? This had never occurred to me. I had always thought of success in terms of quantity, not aesthetics.

How we frame a question matters. Jennifer could have asked, “Why do you want to be successful?” or “How much success is enough?” I would have dismissed those queries, swatted them like the mosquitoes circling as we sat on her deck in New Jersey. Why do I want to be successful? I just do—doesn’t everybody? How much success is enough? More than I currently have.

Jennifer didn’t ask me those questions, though. She asked me what success looked like. Implied in her question was the personal. What does it look like to me? Would I recognize it if I saw it?

I just sat there, stunned, as if a torpedo fish had stung my brain. A good question does that. It grabs hold of you and won’t let go. A good question reframes the problem so that you see it in an entirely new light. A good question prompts not only a search for answers but a reevaluation of the search itself. A good question elicits not a clever reply but no reply at all. From ancient times, long before Socrates, Indian sages have practiced brahmodya, a competition where contestants aim to articulate absolute truth. The contest always ends in silence. As author Karen Armstrong explains, “The moment of insight came when they realized the inadequacy of their words, and thus intuited the ineffable.”

Silence is not my usual state. Words are like oxygen for me. Yet I silently turned Jennifer’s question over in my mind, looked at it from different angles. A good question triggers more questions, and sure enough Jennifer’s single query sparked dozens of my own. I was no longer conversing with her but with myself.

This is exactly what Socrates aimed to induce: a state of ruthless self-interrogation, questioning not only what we know but who we are, in hopes of eliciting a radical shift in perspective.

Tolstoy’s novella The Death of Ivan Ilyich contains one of my favorite passages in literature, perhaps because it is so unexpectedly redemptive, and also involves a train. The protagonist is a successful government official. He is terminally ill, gripped by fear and regret. Toward the end of the story, the dread lifts, replaced by a new perspective “like the sensation one sometimes experiences in a railway carriage when one thinks one is going backwards while one is really going forwards and suddenly becomes aware of the real direction.”

Looking back at my conversation with Jennifer, I realize how I, like Ivan, suddenly intuited my real direction. It was the most Socratic experience I’ve ever had. It took place not in the dusty streets of ancient Athens but on my friend’s deck in Montclair, New Jersey. No matter. Genuine wisdom isn’t bound by place and time. It’s portable.

Now, whenever I’m striving to achieve something, anything, I stop and ask: What does success look like? To be honest, I haven’t answered that question, and may never do so. That’s okay. I’ve changed the prescription on my glasses, and can see more clearly.

The doors glide open. I step into a sleek subway car, shiny and metallic. In modern Greek parlance, I am embarking on a metaforá. Derived from the ancient root metamorphoo, to transform completely from the inside out, it is where we get the English word “metaphor.” Today, Greeks use metaforá to denote travel on public transport. Whenever someone takes a bus to work or the subway to meet friends or a streetcar to pick up dry cleaning, she is, in a way, taking a metaphor, and engaging in a transformative act. I love Greece. Everything exists on two levels, often more. Even a subway ride offers the promise of self-renewal.

Not only does the Athens subway run smoothly, but a history lesson comes with each ride. When it was under construction, workers unearthed ancient artifacts from the city’s golden age. Archaeologists removed some of the artifacts (“rescue archaeology,” it’s called) but others were incorporated into the stations, so that today locals call their subway “a museum with a train running through it.”

I have come to Greece, the land of metaphors, to walk where Socrates walked, to breathe the air he breathed. I have come to remind myself that Socrates was not an idea but a man, flesh and bone. Socrates wondered, but he didn’t wonder just anywhere. He wondered here, in Athens, a city he loved like no other.

I disembark at the Agora Station and walk. The agora, or marketplace, was Socrates’s favorite haunt. It was a crowded and smelly place, rife with hawkers and thieves and everyone else. Socrates loved it. The agora was his classroom, and his theater.

Archaeologists began excavating the site relatively late, in 1931, decades after other big digs, including those at Pompeii and Olympia. They’ve made up for lost time, though, as the thousands of artifacts recovered attest: pottery shards, inscriptions, sculptures, coins, and other ancient treasures.

Today the site, spread over two dozen acres, is mostly rubble, but enough remains of the old marketplace that, with a bit of imagination, I can picture the scene. I can see hawkers selling their wares, everything from spices to water clocks; defendants awaiting trial; young men loitering, as young men do. Taking it all in is Socrates, barefoot, those crablike eyes swiveling wildly, on the prowl for philosophical companions. Socrates practiced retail philosophy. He didn’t wait for people to come to him. He went to them.

“The unexamined life is not worth living,” Socrates famously said. When I first heard that, as a mopey teenager, I sighed. Life is difficult enough. You want me to examine it, too? The examined life. I don’t care for the term. For starters, it contains the root “exam,” which stirs dormant memories of number-two pencils and cold doctor hands. It sounds like too much work. We can do better. So, with all due respect, I offer two corollaries to Socrates’s examined life.

Corollary Number One: The examined life that doesn’t produce practical results isn’t worth living. Contemplating one’s navel has its pleasures but it is far more satisfying to see results, a better navel. Eudaimonia, the Greeks called it. Often translated as “happiness,” the word signifies something larger: a flourishing, meaningful life. Consider, as the contemporary philosopher Robert Solomon suggests, two people. One has an elaborate theory of generosity, while the other does not. “Generosity just flows from him, unthinkingly, as water flows from a fountain.” The second person is clearly leading the exemplary, meaningful life.

Corollary Number Two: The unexamined life may not be worth living, but neither is the overexamined one. “Ask yourself if you are happy and you cease to be so,” said the British philosopher John Stuart Mill, articulating the Pleasure Paradox (also known as Paradox of Hedonism). The more we try to seize happiness the more it slips from our grasp. Happiness is a by-product, never an objective. It’s an unexpected windfall from a life lived well.

So was Socrates wrong about this whole unexamined life nonsense? Or am I missing something?

My instinct is to answer those questions quickly so I can scratch them off my to-do list and move on. I restrain this impulse. Instead, I let the question loiter in the soft Greek air, unanswered but not unexamined. Then I take a metaphor back to my hotel.

Socrates was a failure. I know that sounds harsh, but it’s true. Many of the dialogues end not with a thunder-of-Zeus breakthrough but an impasse. Philosophy produces more problems than it solves. That is its nature.

Socrates didn’t publish, and he perished, executed by his fellow Athenians. Again, his alleged crimes were impiety and corrupting the youth but, really, he was executed for asking too many impertinent questions. He was philosophy’s first martyr.

After his trial, his fate sealed, he gathered with a few of his followers. They were heartbroken, but not Socrates; he remained sanguine, and coyly opaque, until the end. “And now it is time to go, I to die, and you to live, but which of us goes to a better thing is unknown to all but God,” he said.

Those are excellent last words, and indeed that is how many a biography of Socrates ends. There’s only one problem. They were not the philosopher’s last words. Plato, in a dialogue called Phaedo, tells us what transpired during Socrates’s final minutes.

“Crito,” says Socrates, speaking to his friend. “We owe a rooster to Asclepius; make this offering to him and do not forget.”

“It shall be done,” replied Crito. “But have you anything else to say?”

There was no reply. Socrates was dead.

What to make of this seemingly pedestrian exit? For centuries, scholars have pondered that question. Some interpret Socrates’s last words darkly. At the time, roosters were offered to the god of healing, Asclepius, so perhaps Socrates was saying life is like a disease we must cure. Or maybe it was Socrates’s way of calling us back down to earth, even as he ascended to heaven. Maybe he was reminding us, as we grapple with life’s big questions, not to forget the small stuff. Don’t overlook your obligations as a citizen and a friend. Be a person of honor. If you owe someone a rooster, give him a rooster.

There’s a simpler and less profound possibility: the hemlock had begun to take effect, and an addled Socrates was mumbling gibberish. No one knows for certain, and probably no one ever will.

I do know this: it is deliciously fitting that the King of Questions departed in a cloud of them, leaving us scratching our heads, wondering. Socrates couldn’t resist planting one more puzzle in our minds. One more question to experience.